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How to get fromChicago to Highlandby plane, train, train (Amtrak), bus (Flixbus), or car

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There are 9 ways to get from Chicago to Highland by plane, train, train (Amtrak), bus (Flixbus), or car

Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.

  1. Fly Chicago Midway International Airport to Laguardia Airport, train

    best
    1. Fly from Chicago Midway International Airport (MDW) to Laguardia Airport (LGA)plane plane MDW - LGA
    2. Take the train from 125th Street - Harlem to Poughkeepsietrain train
    7h 24m
    $224–591

  2. Fly Chicago O'Hare International Airport to Westchester County Airport, train

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Westchester County Airport (HPN)plane plane ORD - HPN
    2. Take the train from 125th Street - Harlem to Poughkeepsietrain train
    9h 30m
    $126–550

  3. Train (Amtrak)

    1. Take the train from Chicago Union Station to Poughkeepsie Amtrak Stationtrain train Lake Shore Limited
    19h 55m
    $283–579

  4. Bus

    1. Take the bus from Chicago Bus Station to New York Midtownbus bus FlixBus N2641 / ...
    2. Take the bus from TransCenter to Metro North Stationbus bus Wpp
    23h 10m
    $148–250

  5. Drive 810.7 mi

    1. Drive from Chicago to Highlandcar car 810.7 mi
    13h 30m
    $148–214

  6. Fly Chicago O'Hare International Airport to Laguardia Airport, train

    1. Fly from Chicago O'Hare International Airport (ORD) to Laguardia Airport (LGA)plane plane ORD - LGA
    2. Take the train from 125th Street - Harlem to Poughkeepsietrain train
    7h 44m
    $234–691

  7. Fly Chicago O'Hare International Airport to Newark Liberty International Airport, train

    1. Fly from Chicago O'Hare International Airport (ORD) to Newark Liberty International Airport (EWR)plane plane ORD - EWR
    2. Take the train from Ny Moynihan Train Hall At Penn Station to Poughkeepsie Amtrak Stationtrain train
    8h 12m
    $166–933

  8. Fly Chicago Midway International Airport to Albany County Airport, train

    1. Fly from Chicago Midway International Airport (MDW) to Albany County Airport (ALB)plane plane MDW - ALB
    2. Take the train from Albany-Rensselaer Amtrak Station to Poughkeepsie Amtrak Stationtrain train
    8h 16m
    $162–918

  9. Fly Chicago O'Hare International Airport to Albany County Airport, train

    1. Fly from Chicago O'Hare International Airport (ORD) to Albany County Airport (ALB)plane plane ORD - ALB
    2. Take the train from Albany-Rensselaer Amtrak Station to Poughkeepsie Amtrak Stationtrain train
    8h 43m
    $132–768

Chicago to Highland by train and bus (Amtrak)

Calendar7Weekly Services
Duration19h 55mAverage Duration
Ticket$283Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Highland.ExpandLaunch map view
  • Distance: 812.5 mi
  • Duration: 7h 24m

What companies run services between Chicago, IL, USA and Highland, NY, USA?

Amtrak operates a train from Chicago Union Station to Poughkeepsie Amtrak Station once daily. Tickets cost $280–600 and the journey takes 18h 43m. Alternatively, you can take a bus from Chicago Bus Station to Milton Ave. & Vinyard Ave. via New York Midtown, White Plains Station, TransCenter, and Poughkeepsie Train Station in around 23h 10m.

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